10 questions for WellDoc CFO Jon Brilliant

Time with company: board of directors when founded, became CFO 3 years ago.

Education: Bachelor's degree in accounting from The Pennsylvania State University and a graduate degree, Juris Doctor, from Duke University

Company headquarters: Baltimore

Countries of operation: U.S., India

Number of employees total: 105

Number of employees the CFO oversees: 5

CFO's areas of responsibility: finance, HR, legal

About the company: WellDoc, a health-care behavioral science and technology company, develops and offers software and services that help patients and doctors manage chronic diseases.

1. Where did you start in finance and what experiences led you to the job you have today?

I began my professional career at Arthur Andersen and then went back to graduate school, and I think what really led me to finance was more my frustration than anything. I was a deal and transactional lawyer, where I did everything from restructuring the entire debt of the country of Bolivia to the IPOs of Office Max and Borders. Along the way, I found myself wanting to provide business advice and became very frustrated with the attitudes that, "those are just business issues not legal, and we don't need your help with that."

I was with JM Family Enterprises, with about 10 billion revenue, with a small group -- this was in '97, the Internet was booming and we started building different business models for how we could leverage the Internet within our business. We were the largest privately held distributor of Toyota cars and parts. It was there that I was able to apply what I wanted to apply, but hadn't been able to because people would say, "you're just a lawyer."

When we took our ideas to management, they did what management does when employees come up with great ideas -- they went and hired a consultant. We spent more than a million dollars with Cambridge Consulting Partners and they validated what we had come up with. So management said if you're so smart, we'll let you be chief Web officer, so that's really when I started to manage business.

2. Who was an influential boss for you and what lessons did they teach you about management and leadership?

The person I will name, who has passed away, I'm sure would be proud to be named and that is a gentleman by the name of Jim Moran. Jim was a self-made Horatio Alger Award winner from Chicago. He founded and ran JM Family.

There were two fundamental things that stick with me to this day that Jim taught me. One is just how to manage a business. He went back to his roots in gas-station accounting for that. We did billions of dollars in finance and loans in different states and all he came back to every day was gas-station accounting. What he taught me was that you know how much money you have in the bank when you start each morning, you should know how much it costs you to turn on the lights every day, so at the end of the day, if you have the same amount of money or more in the bank, it's a good day.

I learned very quickly that profit is an opinion, but cash is a fact. Managing a business through cash became a fundamental principle through which I operate.

On the leadership side, what I learned is that it's fundamentally how you treat people. We were all associates at JM Family -- we were not employees. Jim always believed that you come to work with people, not for people. That sets the tone for how you think of yourself as a leader.

It's an old cliché, possibly, but I think it's very difficult to hire people who are smarter than you and get out of their way and let them do their job. Be proud to work with them and be associated with them, but get out of their way. Don't lead by fiat. It's about empowering people and supporting them to do what they need to do.

The last principle I learned is that good news should travel fast, but bad news should travel faster. If those problems don't come to light until the end, you're often left with not enough time. I think it's important to encourage people to bring forth bad news, not just good news.

3. What are the biggest challenges facing CFOs today?

Part of it depends on your definition of a CFO. There was a Harvard Business Review article written about this and it talked about the changing role of a CFO and I think the CFO role has changed dramatically to be much more strategic and much less nuts and bolts. As a result, I think the biggest challenge a CFO has in any organization, ours included, is assessing risk, whether it be market risk, external factors or internal risk.

I've had a lot of experience in an investor role and I think another huge challenge in the CFO space is to assess the skill sets that someone has against the role that we're putting them in. We look at them, we watch them and then when they fail we say they can't do their job. But on the front end we didn't properly assess that person or give them the right opportunity to learn those skills. I think risk internally is all about execution so that you have the right people in the right seat, doing the right thing at the right time.

4. What is a good day at work like for you?

One [example is] looking inward and one is looking outward.

One looking inward is that the biggest stress in life is having things on your to-do list that you never accomplish, so to me a good day is setting out to accomplish three or four things on my to-do list. I have a long-term to-do list and a short-term to-do list, and if I get to one on the long-term list and one on the short-term list, that's a good day. There are often distractions, so I try to spend time reflecting at the beginning of the day on what I need to accomplish and at the end of the day on what did I accomplish.

And looking outward another good day for me is watching the people who work with me shine, whether it's as simple as making a presentation at a meeting or announcing a customer win, I think it's important to share in other people's success. I think it's a good day when people around you are feeling accomplished.

5. How would you characterize your management style?

Again, I think for me, it's making sure that someone understands what they're supposed to do and giving them all the tools, whether it be a computer or information or training, it really is allowing people to do their jobs.

To me, your job is like an interview -- you're almost every day conducting an interview, asking "am I the right person for this job?" I make sure I'm supporting people and giving them all they need so they can't say, "You didn't tell me something or you didn't give me the tools to do something, so I can't do what I need to do." I give them what they need and get out of the way and let people do their job.

6. What strengths and qualities do you look for in job candidates?

Having made many, many mistakes in hiring people and watching the lessons learned, I think for me it comes down to what I'll call intellectual curiosity. You really want to hire someone who is intellectually curious, who has a willingness and a desire to ask questions, who is not afraid to ask questions, who is not afraid to change the status quo. To me, that is the single biggest factor.

You're not a robot, you're not a machine. Associates should be able to challenge and ask questions and be curious. I think that's the single biggest quality -- certainly also I look for honesty and integrity and all of those things that are givens, but to me that one -- intellectual curiosity -- stands above all.

7. What are some of your favorite interview questions or techniques to elicit information to determine whether a candidate will be successful at your company? What sort of answers send up red flags for you and make you think a job candidate wouldn't be a good fit?

One of the first questions I always ask early on is, "have you fired someone?" It shows a willingness to challenge the status quo and to make changes whenever changes need to be made. I think that's important. There's some shock value when I ask that question. People will say, "why did you ask that?"

From a purely personal standpoint, when I was at Arthur Andersen, Wayne McCune had a simple test that has stuck with me to this day. He called it the "airplane test": Imagine that you're sitting next to someone on an airplane and you're stuck on the tarmac and the plane doesn't take off for four or five hours and then you have a two-hour flight, so you've spent six or seven hours with that person. When you land, would you exchange contact information with them, is this someone you would want to be in a difficult situation with? Can they tell jokes or are they stressed?

It's the proverbial notion that we spend more hours at work than we do with our family, unfortunately, at times.

For me, interviewing is also having a conversation, so one of the things I look for is how comfortable someone is in their own skin, do they have canned answers or are they comfortable just having a conversation. Even under stress people can be people and have conversations. I think that's important.

And are they a good storyteller? Storytelling is an important attribute because we need to be able as associates to talk to each other. I look for people who can tell a good story and who can put their life experiences and their work experiences in the context of a story.

I also look for people, and this is hard to tell in an interview, who are self-actualized. Was there a time when you made a mistake, when you didn't do what was right and you recognize and acknowledge these? You need to reward failure and let people feel comfortable with failing. To have someone who is willing to admit, "I failed, I didn't succeed," that is very revealing, that is the sort of person who is going to put up their hand and say, "I have a question, I need more information."

Some individuals don't want to admit that they don't know everything, they are afraid that this might show they are not the right person for the job, but it's actually the reverse.

8. What is it about your current job, at this particular company, that sets it apart from other chief finance positions?

The single biggest thing that we face is that we're blazing new paths. When we did our first clinical trial back in 2005, we set out to do it as a proof of concept, to prove that someone would use their mobile phone to manage their chronic disease, in this case diabetes. The critique we got is that we were not sure that people would use data applications on cellphones. At the time, we didn't know the iPhone was coming, we didn't know that smartphones were coming.

All along the way, we've been faced with blazing the path of answering the question of will people use data applications, will you get clinical trial outcomes, will someone pay for this? We've always been pioneers, so what challenges you in the finance role is to balance when market adoption will occur and gain traction against the cash needs of the business. Is now the time to invest in the business and put expenses ahead of revenue?

At WellDoc, we're trying to figure out new ways to get paid, how do doctors use our product, how do health-care providers use our product.

There are big implications to that business model for how we finance ourselves, how we manage cash. That pioneering, disruptive business model is challenging. When you're pioneers you can be the guy facedown in the mud with an arrow in his back or you can continue to be the leader and show a path for others to follow.

9. What do you do to unwind from a hectic day?

Go for a long run or sit quietly on my front porch with my family.

10. If you weren't doing this job, what would you be doing?

I think if I had to continue to pay bills I would most likely go back and be a venture capitalist. I am enamored with nurturing startups and companies and helping them perform with the best model they can. I'm fascinated by entrepreneurs and new businesses that people come up with.

If I didn't have bills to pay, I'd be teaching tennis. I played tennis at Penn State when I was an undergraduate.

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